CH648307A5 - Verfahren zur herstellung von 3-(n-aryl-n-acyl-amino)-gamma-butyrothiolactonen. - Google Patents

Verfahren zur herstellung von 3-(n-aryl-n-acyl-amino)-gamma-butyrothiolactonen. Download PDF

Info

Publication number: CH648307A5
Authority: CH; Switzerland
Prior art keywords: lower alkyl; formula; group; meaning; bromine
Prior art date: 1980-06-23

Application number

CH4154/81A

Other languages

German (de)

English (en)

Inventor

Francis J Freenor Iii

David C K Chan

Stephen D Ziman

Original Assignee

Chevron Res

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-06-23

Filing date

1981-06-23

Publication date

1985-03-15

1980-09-08 Priority claimed from US06/184,846 external-priority patent/US4311849A/en

1981-06-23 Application filed by Chevron Res filed Critical Chevron Res

1985-03-15 Publication of CH648307A5 publication Critical patent/CH648307A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 3
125000000217 alkyl group Chemical group 0.000 claims description 89
-1 2,6-dimethylphenylamino Chemical group 0.000 claims description 83
238000000034 method Methods 0.000 claims description 66
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 54
150000001875 compounds Chemical class 0.000 claims description 47
239000000203 mixture Substances 0.000 claims description 47
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 30
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 30
229910052794 bromium Inorganic materials 0.000 claims description 30
239000000460 chlorine Substances 0.000 claims description 30
229910052801 chlorine Inorganic materials 0.000 claims description 30
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 29
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 21
125000003545 alkoxy group Chemical group 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 21
229910052731 fluorine Inorganic materials 0.000 claims description 20
239000011737 fluorine Substances 0.000 claims description 20
239000003795 chemical substances by application Substances 0.000 claims description 19
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
239000003960 organic solvent Substances 0.000 claims description 17
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 16
125000003342 alkenyl group Chemical group 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 14
239000007858 starting material Substances 0.000 claims description 13
150000001266 acyl halides Chemical class 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 12
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 12
239000007788 liquid Substances 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 7
150000003138 primary alcohols Chemical class 0.000 claims description 7
125000003107 substituted aryl group Chemical group 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 6
125000003302 alkenyloxy group Chemical group 0.000 claims description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
125000001769 aryl amino group Chemical group 0.000 claims description 6
239000012876 carrier material Substances 0.000 claims description 6
238000005917 acylation reaction Methods 0.000 claims description 5
230000032050 esterification Effects 0.000 claims description 5
238000005886 esterification reaction Methods 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical group COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 claims description 4
230000010933 acylation Effects 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
150000001735 carboxylic acids Chemical class 0.000 claims description 3
235000014113 dietary fatty acids Nutrition 0.000 claims description 3
239000000194 fatty acid Substances 0.000 claims description 3
229930195729 fatty acid Natural products 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
239000011630 iodine Substances 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 2
150000004665 fatty acids Chemical class 0.000 claims description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 2
OROGUZVNAFJPHA-UHFFFAOYSA-N 3-hydroxy-2,4-dimethyl-2H-thiophen-5-one Chemical compound CC1SC(=O)C(C)=C1O OROGUZVNAFJPHA-UHFFFAOYSA-N 0.000 claims 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims 2
125000004970 halomethyl group Chemical group 0.000 claims 2
150000004671 saturated fatty acids Chemical class 0.000 claims 2
150000001768 cations Chemical class 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
239000000047 product Substances 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
239000000417 fungicide Substances 0.000 description 14
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 13
230000000855 fungicidal effect Effects 0.000 description 13
239000011734 sodium Substances 0.000 description 12
229910052708 sodium Inorganic materials 0.000 description 12
239000002904 solvent Substances 0.000 description 12
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000000376 reactant Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
150000001263 acyl chlorides Chemical class 0.000 description 8
239000003921 oil Substances 0.000 description 8
238000009472 formulation Methods 0.000 description 7
239000007787 solid Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000002270 dispersing agent Substances 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
208000031888 Mycoses Diseases 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
206010017533 Fungal infection Diseases 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
238000011065 in-situ storage Methods 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
TUZFIWBNGKNFPW-UHFFFAOYSA-M sodium;2-methylpropane-2-thiolate Chemical compound [Na+].CC(C)(C)[S-] TUZFIWBNGKNFPW-UHFFFAOYSA-M 0.000 description 4
150000007944 thiolates Chemical class 0.000 description 4
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
241000233866 Fungi Species 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
BKPXEDRKBBTGAQ-UHFFFAOYSA-N 4-(2,6-dimethylanilino)oxolan-2-one Chemical compound CC1=CC=CC(C)=C1NC1CC(=O)OC1 BKPXEDRKBBTGAQ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
235000008733 Citrus aurantifolia Nutrition 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
235000011941 Tilia x europaea Nutrition 0.000 description 2
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000005452 alkenyloxyalkyl group Chemical group 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
229930188620 butyrolactone Natural products 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000000428 dust Substances 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
125000003700 epoxy group Chemical group 0.000 description 2
238000000605 extraction Methods 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
239000004571 lime Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000002002 slurry Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
239000003053 toxin Substances 0.000 description 2
231100000765 toxin Toxicity 0.000 description 2
238000005406 washing Methods 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ZBRWJPVULTZZCE-UHFFFAOYSA-N 1-propylsulfanylbutane Chemical class CCCCSCCC ZBRWJPVULTZZCE-UHFFFAOYSA-N 0.000 description 1
MTOBBJCWGZMHGE-UHFFFAOYSA-N 2-(2,6-dimethylphenoxy)acetyl chloride Chemical compound CC1=CC=CC(C)=C1OCC(Cl)=O MTOBBJCWGZMHGE-UHFFFAOYSA-N 0.000 description 1
AAWZWSVNYNIBHJ-UHFFFAOYSA-N 2-(4-ethoxyphenoxy)acetyl chloride Chemical compound CCOC1=CC=C(OCC(Cl)=O)C=C1 AAWZWSVNYNIBHJ-UHFFFAOYSA-N 0.000 description 1
LCIMJULVQOQTEZ-UHFFFAOYSA-N 2-hydroxyacetyl chloride Chemical compound OCC(Cl)=O LCIMJULVQOQTEZ-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
BIQVQVGFZQXERD-UHFFFAOYSA-N 3-methyloxirane-2-carbonyl chloride Chemical compound CC1OC1C(Cl)=O BIQVQVGFZQXERD-UHFFFAOYSA-N 0.000 description 1
HXPSOFMRBFXPDW-UHFFFAOYSA-N 3-oxopent-4-enoyl chloride Chemical compound ClC(=O)CC(=O)C=C HXPSOFMRBFXPDW-UHFFFAOYSA-N 0.000 description 1
JLPLJLLOCNCVTA-UHFFFAOYSA-N 4-bromooxolan-2-one Chemical compound BrC1COC(=O)C1 JLPLJLLOCNCVTA-UHFFFAOYSA-N 0.000 description 1
JVVBLWPCBNOZQC-UHFFFAOYSA-N 4-tert-butylsulfanyl-2-(2,6-dimethylanilino)butanoic acid Chemical compound C(=O)(O)C(CCSC(C)(C)C)NC1=C(C=CC=C1C)C JVVBLWPCBNOZQC-UHFFFAOYSA-N 0.000 description 1
XJWALMVUXRWVKI-UHFFFAOYSA-N 4-tert-butylsulfanyl-2-(N-(2-methoxyacetyl)-2,6-dimethylanilino)butanoic acid Chemical compound C(=O)(O)C(CCSC(C)(C)C)N(C(COC)=O)C1=C(C=CC=C1C)C XJWALMVUXRWVKI-UHFFFAOYSA-N 0.000 description 1
GXUUQSDGACQISL-UHFFFAOYSA-N 4-tert-butylsulfanylbutanoyl 4-tert-butylsulfanylbutanoate Chemical compound C(C)(C)(C)SCCCC(=O)OC(CCCSC(C)(C)C)=O GXUUQSDGACQISL-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
240000007124 Brassica oleracea Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
241000549404 Hyaloperonospora parasitica Species 0.000 description 1
235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
241000233614 Phytophthora Species 0.000 description 1
241000233622 Phytophthora infestans Species 0.000 description 1
241001281803 Plasmopara viticola Species 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
240000003768 Solanum lycopersicum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
241000219094 Vitaceae Species 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001262 acyl bromides Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
150000001767 cationic compounds Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000011362 coarse particle Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000013068 control sample Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
PYFRLDVYGBCYLI-UHFFFAOYSA-N decyl dihydrogen phosphite Chemical compound CCCCCCCCCCOP(O)O PYFRLDVYGBCYLI-UHFFFAOYSA-N 0.000 description 1
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
235000021021 grapes Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
229910001411 inorganic cation Inorganic materials 0.000 description 1
229910003480 inorganic solid Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
235000014666 liquid concentrate Nutrition 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
235000011160 magnesium carbonates Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000035515 penetration Effects 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
239000001294 propane Substances 0.000 description 1
GLBUZFYJIIWCFB-UHFFFAOYSA-N propanethioyl chloride Chemical compound CCC(Cl)=S GLBUZFYJIIWCFB-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000000523 sample Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
235000001508 sulfur Nutrition 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
125000004417 unsaturated alkyl group Chemical group 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

CH4154/81A 1980-06-23 1981-06-23 Verfahren zur herstellung von 3-(n-aryl-n-acyl-amino)-gamma-butyrothiolactonen. CH648307A5 (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US16245380A	1980-06-23	1980-06-23
US06/184,846 US4311849A (en)	1980-09-08	1980-09-08	Process for making 3-(N-arylamino)-gamma-butyrothiolactones
US20086480A	1980-10-27	1980-10-27

Publications (1)

Publication Number	Publication Date
CH648307A5 true CH648307A5 (de)	1985-03-15

Family

ID=27388753

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH4154/81A CH648307A5 (de)	1980-06-23	1981-06-23	Verfahren zur herstellung von 3-(n-aryl-n-acyl-amino)-gamma-butyrothiolactonen.

Country Status (8)

Country	Link
CH (1)	CH648307A5 (es)
DD (3)	DD203718A5 (es)
DE (1)	DE3123864A1 (es)
ES (3)	ES8300105A1 (es)
FR (3)	FR2485013A1 (es)
GB (1)	GB2078741B (es)
IT (1)	IT1136849B (es)
NL (1)	NL8103024A (es)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5175310A (en) *	1990-03-16	1992-12-29	Elf Atochem North America, Inc.	Process for producing alkylthio- and arylthio-substituted carboxylic acids and their thioesters
CN1035252C (zh) *	1993-11-23	1997-06-25	王桂英	氨甲基甲酸-1，1，1-三氯-2-(2,4－二氯硫酚基) 乙基酯及其制备方法
ES2088817B1 (es) *	1993-12-02	1997-08-01	Univ La Laguna	Control de nematodos fitoparasitos con lignanos tipo dibencil-butirolactonas.
CN112724403B (zh) *	2019-10-14	2022-10-04	中国科学院上海有机化学研究所	聚(γ-硫代丁内酯)及其制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2408601A1 (fr) *	1977-11-01	1979-06-08	Chevron Res	Procede d'acylation d'une aniline substituee par une lactone en l'absence d'accepteur d'acide
BR8000986A (pt) *	1979-02-22	1980-10-29	Chevron Res	Composto fungicida, processo para controlar o crescimento de fungos, composicao fungicidas e processo para o controle de fungos
MA19111A1 (fr) *	1979-10-26	1981-12-31	Ciba Geigy Ag	Derives de l'homoserine,procede pour leur preparation et leur utilisation en tant que microbicides

1981
- 1981-06-16 DE DE19813123864 patent/DE3123864A1/de not_active Withdrawn
- 1981-06-19 FR FR8112167A patent/FR2485013A1/fr active Granted
- 1981-06-22 IT IT22482/81A patent/IT1136849B/it active
- 1981-06-23 DD DD81244216A patent/DD203718A5/de unknown
- 1981-06-23 GB GB8119334A patent/GB2078741B/en not_active Expired
- 1981-06-23 NL NL8103024A patent/NL8103024A/nl not_active Application Discontinuation
- 1981-06-23 CH CH4154/81A patent/CH648307A5/de not_active IP Right Cessation
- 1981-06-23 DD DD81244217A patent/DD209443A5/de unknown
- 1981-06-23 DD DD81231058A patent/DD160416A5/de unknown
- 1981-06-23 ES ES503313A patent/ES8300105A1/es not_active Expired
- 1981-11-17 FR FR8121477A patent/FR2491062A1/fr active Granted
- 1981-11-17 FR FR8121478A patent/FR2491069B1/fr not_active Expired
1982
- 1982-06-14 ES ES513070A patent/ES8304114A1/es not_active Expired
- 1982-06-14 ES ES513071A patent/ES8304115A1/es not_active Expired

Also Published As

Publication number	Publication date
FR2491069A1 (es)	1982-04-02
ES513071A0 (es)	1983-02-16
FR2491062B1 (es)	1985-01-18
GB2078741A (en)	1982-01-13
FR2485013A1 (fr)	1981-12-24
GB2078741B (en)	1984-02-08
ES8304115A1 (es)	1983-02-16
ES513070A0 (es)	1983-02-16
FR2485013B1 (es)	1984-06-29
IT1136849B (it)	1986-09-03
ES503313A0 (es)	1982-10-01
DE3123864A1 (de)	1982-03-04
FR2491062A1 (fr)	1982-04-02
DD160416A5 (de)	1983-07-27
IT8122482A0 (it)	1981-06-22
FR2491069B1 (es)	1983-12-16
ES8300105A1 (es)	1982-10-01
DD203718A5 (de)	1983-11-02
ES8304114A1 (es)	1983-02-16
DD209443A5 (de)	1984-05-09
NL8103024A (nl)	1982-01-18

Legal Events

Date	Code	Title	Description
1988-02-29	PL	Patent ceased

Publication	Publication Date	Title
EP0337263B1 (de)	1993-03-17	Isoxazol(Isothiazol)-5-carbonsäure-amide
DE2804299A1 (de)	1978-08-10	Fungizide mittel
EP0418667A2 (de)	1991-03-27	Carbonsäureamide
DE3713774A1 (de)	1987-10-29	Neue pyrazol-derivate, verfahren zu ihrer herstellung und fungizide fuer landwirtschaft und gartenbau, welche diese verbindungen enthalten
EP0388873B1 (de)	1994-05-11	Herbizide [[1,3,5-Triazin-2-yl) aminocarbonyl] aminsulfonyl] benzoesäureester, Verfahren zu ihrer Herstellung und ihre Verwendung
DE4318917A1 (de)	1994-12-08	2-Oximino-2-phenyl-acetamide
EP0332009A1 (de)	1989-09-13	N-Aryltetrahydrophthalimidverbindungen
CH648307A5 (de)	1985-03-15	Verfahren zur herstellung von 3-(n-aryl-n-acyl-amino)-gamma-butyrothiolactonen.
EP0378092B1 (de)	1994-05-11	Herbizide Sulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung
EP0257294B1 (de)	1990-09-12	E/Z-Isomerengemische und reine Z-Isomere von N alpha-(2-Cyan-2-alkoximinoacetyl) aminosäurederivaten und- peptiden
WO1993010095A1 (de)	1993-05-27	Substituierte pyridin-4-carbonsäureamide und ihre verwendung zum schutz von pflanzen gegen befall durch mikroorganismen
EP0379003A1 (de)	1990-07-25	Thiophen-2-carbonsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
EP0072970A1 (de)	1983-03-02	Substituierte Anilinomethylen-oxime, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Pflanzenschutzmittel
EP0419917B1 (de)	1994-11-17	Pyrazol-3-carbonsäureamide
EP0398059B1 (de)	1993-08-25	Cyclopropanoylaminosäureamid-Derivate
EP0207355A1 (de)	1987-01-07	Alkoxycarbonyl-substituierte Hydroxythiophen-carbonamide
EP0088325B1 (de)	1985-09-11	Oximinoessigsäureamide, ihre Herstellung und ihre Verwendung zur Bekämpfung von Fungi und Mittel dafür
EP0493721B1 (de)	1997-05-14	Styrolderivate
DE2846038A1 (de)	1980-05-08	1,2,4-triazolderivate, ihre herstellung und verwendung
EP0046931A2 (de)	1982-03-10	N-Oxiamide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide
EP0040310A2 (de)	1981-11-25	Fungizide, heterocyclisch substituierte Thioglykolsäureanilide, Verfahren zu ihrer Herstellung und diese enthaltende Schädlingsbekämpfungsmittel
DE3041998A1 (de)	1982-06-09	Pyrazolsubstituierte oximino-cyan-acetamid-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
EP0087048B1 (de)	1985-04-17	Substituierte Oximinoacetanilide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Schädlingsbekämpfungsmittel
AT379152B (de)	1985-11-25	Verfahren zur herstellung von 3-(n-aryl-nacylamino)-gamma- butyrothiolactonen
DE3719225A1 (de)	1988-12-22	(2-cyan-2-methoximinoacetyl)-aminosaeure- derivate